


Oh my gosh!

by CrittersweetSymphony



Category: Critical Role (Web Series)
Genre: Dry Humping, F/M, First Kiss, First Time, Masturbation, Slow Build
Language: English
Status: Completed
Published: 2020-09-05
Updated: 2020-09-05
Packaged: 2021-03-06 16:28:01
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,980
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26301928
Author URL: https://archiveofourown.org/users/CrittersweetSymphony/pseuds/CrittersweetSymphony
Summary: Even though she grew up within the walls of The Lavish Chateau and was familiar with many sexual practices, having seen plenty of goings on first-hand, she’d never even kissed anyone before so had little understanding of the actual practicalities in the bedroom.What she needed was a confidante, someone to answer all the questions running around her head.
Relationships: Jester Lavorre/The Traveler
Comments: 2
Kudos: 51





	Oh my gosh!

Jester had spent the entire morning on board the decks of The Balleater making herself look busy, as if she were carrying out some super important repairs to the ship. Truth be told, she couldn’t keep her eyes off Fjord as he assumed his role of Captain, leading the rest of the crew in their day to day duties, setting the navigational course and ensuring Nott didn’t blow up the ship with her more than enthusiastic endeavours on the gun deck.

She couldn’t help herself. She was besotted with his air of confidence, his athletic and toned physique, the little suggestion of his tusks starting to regrow, and the way he would always look out for her, would always have her back. She just knew though that it was never meant to be. He clearly went for women with more experience, like Captain Avantika, who oozed sex appeal and the slightest hint of danger. Jester just didn’t compare and was vastly inexperienced when it came to her sexual prowess. 

Even though she grew up within the walls of The Lavish Chateau and was familiar with many sexual practices, having seen plenty of goings on first-hand, she’d never even kissed anyone before so had little understanding of the actual practicalities in the bedroom. What she needed was a confidante, someone to answer all the questions running around her head. Maybe, if she had more info, she’d feel more confident and could sweep Fjord off his feet in a romantic embrace some evening on the outer deck as the sun set. 

Determined to complete this mission, Jester took herself off to her cabin below deck, with Beau otherwise occupied at the helm with Fjord, hopped up on her bed, holy symbol in hand.

“Traveleeeeeeeer – I need to talk to you! Are you there?”

As each moment passed, listening for a familiar voice – silence.

“Awww man, really? I got to cast a spell for you to come talk to me? Okaaaaay, but if we get in trouble later and all die because I’m totally tapped out then, you know, you’re…gonna be pretty sad.”

She waited, eagerly listening, glancing around the room.

“Gah…okay, okay, okay,” she sighed in frustration, focusing on the symbol she held in her hands, eyes shut tightly, and nose scrunched up as she imagined The Traveler before her, whispering the incantation.

“I do so enjoy our conversations better with eyes open my Jester,” came the warm and comforting response, smooth as caramel as it rolled off his tongue.

Jester peeked one eye open to see her verdant-eyed friend stretched out on Beau’s bed, just an arm’s length away, hands clasped behind his flaming red hair as he reclined, grinning.

“It’s been some time since last we spoke. What wonderous mischief are you plotting in that brilliant mind of yours Jester? Humiliation? Desecration? You’ve certainly got my attention,” he mused, one eyebrow raised and smirking with narrowed eyes.

Thoughts of Fjord popped into her head as she nervously looked down at the holy symbol she rolled in her hands, a violet flush coming to her cheeks as she nibbled on her lower lip.

“Weeell, that’s not exaaactly why I wanted to speak with you Traveler…not exaaactly. I really need some advice and you’re like…well, you’re my best friend and I know I can trust you, and you can keep a secret, and you won’t judge me or make fun of me…” she rambled in her undulating sing-song voice, not knowing where to look, “and, oh my gosh, oh my gosh…I only have three questions. Gah, this is so stupid Traveler! Why can’t we just hang out like when we were little?” she huffed with furrowed brows. “Eeeek,” she squeaked, “that doesn’t count though…that’s not a question…I take it back!” she panicked.

“It’s all right Jester,” he said calmingly. “Whatever it is, I can…maybe show some leniency. A favour for a favour perhaps, given how much you’ve already helped with preparations for our gathering in the coming months.”

She sighed and gently smiled in relief, the tension leaving her shoulders as she looked up at The Traveler bashfully from under her brow.

“Aww man, this is so embarrassing, I mean I know everything already…well…kind of. Like, I’ve read a lot of books about relationships and boning and love and stuff, you know? And at Mama’s I saw pretty much everything that went on and I mean, I saw some preeetty steamy stuff. But I…um…well…I guess I’m maybe not too sure about what exaaactly is nice for a guy or what really turns them on, you know? Like, the stuff you can’t see or read about, what feels good for them you know? Oh gosh, maybe this was a bad idea. Don’t worry about it Traveler…you don’t need to say anything, and we can forget…” she continued, falling back on the bed, covering her face with her arms.

“Jester, oh my Jester…,” the Traveler chuckled making his way to sit at the edge of Jester’s bed, lightly placing his hand on her arm, “…you never need to feel embarrassed in front of me. These are all completely natural thoughts and questions and the truth is, everyone is different. What I like might be vastly different from someone else but what’s most exciting is figuring it out, trial and error, complete delicious chaos until you find what’s right for you both. Practice makes perfect!”

Jester slowly began to raise her arms, just giving her enough room to see her friend sitting beside her.

“But how do I know if I’m doing it right? Like, how much tongue is too much tongue? How do I know if the pressure is right, if the angle is good for him or if I’m nibbling too hard? Oh my gosh…” and she rolled over on her side, shying away from The Traveler, mortified at the questions she was asking out loud. 

“Well, I mean, asking is always an option, though it caaan be a bit of a buzz kill in the moment. It’s not something I’ve really thought about, per se, but I guess the simple way is to read the cues, the tell-tale signs,” he pondered thoughtfully, running his thumb back and forth across Jester’s shoulder.

“But that’s the problem, I don’t know what to look out for, well, other than his dick getting hard, I mean…that’s a preeetty good sign,” she giggled, looking back at him over her shoulder, wagging her eyebrows in the suggestive fashion he’d come to know and love.

“Ah, yes, well you’re not wrong Jester. That certainly is an indication of ah, optimal pleasure shall we say? But you’ll soon come to know all the other delectable responses the body is so very capable of,” he whispered, bringing his hand down her arm before lifting and rejoining his other in his lap.

A shiver ran down Jester’s spine at his touch, hairs tingling at the back of her neck as she reached out instinctively to hold his arm, pausing for just a moment in thought. 

“Would you show me, Traveler?” she asked, innocent eyes peering up at him from across her shoulder, her teeth worrying the corner of her lip, her chest rising with heavier breaths.

“Ha, Jester, I…I don’t think that would be the wisest…” he stammered, clearly caught off guard by the suggestion of the blossoming, beautiful woman he had come to know lying before him. She really was a sight to behold, from her smooth, dewy skin, the natural curves of her form, to the devilish sparkle in her eye.

Using his arm for support, Jester pulled herself up to a sitting position, slowly turning towards him, her heavy eyes now merely inches away from his sculpted jawline as she ran her gaze upwards to his slightly parted lips, his well-defined cheekbones, finally meeting those vibrant green eyes she had looked into a thousand times before, but not like this. For now she craved his touch, his hands, his lips, their proximity palpable.

Never leaving his gaze, she raised her hand from his arm, gently placing it on his cheek, his fair skin beneath her fingertips as she breathily repeated,

“Show me.”

Pausing pensively for a few moments, The Traveler raised his finger up to rest just barely under her chin. With her eyes headily locked on his, he let his gaze fall to wander along her perfect, button-nose, across her flushed, freckled cheeks, finally resting on her full lips, now glistening where her tongue had moistened them in anticipation. Heart beating in his chest, The Traveler lightly and deftly guided Jester’s head up, tilted his own ever-so-slightly to the side, closed the gap between them and pressed his lips to hers as his eyes closed, taking in every sensation.

Pulling apart slightly after a few moments, foreheads still pressed together, Jester’s breath hitched as her chest rose and fell. His lips were tender, softer than she had imagined yet she could feel her heartbeat beginning to race. She had not intended for this to happen, that she would be…intimate with The Traveler, but the feeling was warm and comforting, a sensation that spread throughout her body and all she knew in that moment was that she desired more.

Bringing her other hand to rest on his chest, she trailed her finger from his cheek to run along his lower lip as she watched the tip of his tongue greet her finger tentatively. She pressed on his tongue lightly and he welcomed her fingertip between his lips, running his tongue beneath with a grin. Her breath catching in her throat, she felt her core begin to twitch and quickly replaced her finger with a second kiss, brushing her tongue lightly against his at first, before they both began exploring each other’s mouths with more intensity.

The feeling was exhilarating and as Jester could feel her arousal building, she wrapped her arms tightly around The Traveler, pressing her chest to his, a whimper escaping between kisses. Knowing this was her opportunity to learn what The Traveler had to teach, she brought her hands to his front, under his cloak brushed it back off his shoulders onto the bed. Pulling back from him momentarily, placing kisses sparingly across his jawline and tenderly beneath his ear, she slid her hands up under his tunic and whispered devilishly,

“Do you mind if I practice some more Traveler? You’ve always been my greatest teacher,” as she tugged lightly on his earlobe between her teeth, sucking it between her lips. He flinched with a shiver and sharp intake of breath. 

“I’ll take that as cue, shall I?” she smirked as he invitingly raised his arms, letting her rid him of his tunic.

“That’s my darling Jester, always such a quick learner and full of surprises!” The Traveler remarked, raising his brow knowingly. “Who am I to deny my brightest student that which brings her pleasure?” 

Still sitting on the edge of the bed, body turned towards Jester, The Traveler leant back, supporting himself with one arm behind him, and guided Jester back in for another kiss, this time more passionate than before, arm around her waist as she pressed against his bare chest. Letting her teeth tug a little on his lower lip, eliciting the most delicious guttural sound from her new play thing, Jester continued to playfully nibble and nip along The Traveler’s neck and collar bone before biting a little harder on his shoulder to leave her mark.

Encouraged by The Traveler’s blissful responses, Jester repositioned herself to kneel before him, bending forwards to slowly lick across his smooth, lithe chest, circling each nipple in turn, watching his expression all the while. Arching his head back as he exhaled, The Traveler brought his hand from Jester’s waist to her head, lightly gripping her hair and pulling her closer to him and she flicked her tongue across his nipple, taking it between her teeth as he gasped. 

“You…darling Jester…are…delightful,” he exclaimed now breathing heavier, a flush across his cheeks and chest. 

With that, he sat up, hooked his hands over and beneath Jester’s thighs and pulled her onto his lap in one swift motion, taking her lips in his as she brought her hands down to the small of his back just dipping below the waistline of his trousers. 

His kisses and movements were needy now as he pulled her close, so close she could feel his excitement through her undergarments as it nudged against her core. Jester knew her own body well and what felt good to her from years of playful experimentation in her room in the Chateau and her journeys with The Mighty Nein. But this was different. Never before had she felt the same rush with another person, and it felt wonderful. So wonderful that she ground her hips down further on The Traveler’s lap to heighten the friction between them.

“Careful my dearest. That…aah, that…is, remarkably effective and aah, might bring…our playtime to an end…all too soon,” The Traveler gasped between panted breaths as he managed to control his urges.

As she nuzzled into the crook of his neck, placing small bites where he seemed most sensitive, Jester brought her hands to his chest once more, pushing him backwards onto the bed playfully, surprising him with her strength. 

“Don’t worry ‘bout it, Traveler. If you cum in your pants we can always have more lessons,” she assured him, now rubbing herself forwards and backwards on his poor, restrained cock as she found just the right angle to tantilise her clit. The sensation now was almost overwhelming as she felt flushed with heat, sweat forming on her brow, her legs beginning to tremble and moistness gathering between her legs.

“Holy shitballs, Traveler,” she exclaimed breathlessly, “Fuck, I think…I think I’m gonna cum!” reaching down under her smallclothes to circle her clit with her fingers, arching her back and looking The Traveler straight in the eye, her mouth open as she made a series of delectable high-pitched whimpers.

Already moments away from his own climax, seeing Jester flushed and in such a state as she gyrated above him along his cock, taking her own pleasure into her own hands, The Traveler could contain himself no longer. He thrust up against Jester in a wonderful, stuttering release,

“Good Gods, Jester – relentless, magnificent Jester,” he panted, breathing heavily and grinning from ear to ear. 

His final thrust and exclamation were enough to send Jester over the edge as she clenched, feeling the sudden familiar gush from her cunt as she came with his name on her lips, still circling her clit as she rode out the last of her orgasm, shaking against The Traveler’s now soaked crotch. 

“Oh my gosh, oh my gosh,” Jester whimpered, falling down on the bed beside The Traveler, hands coming up to bury her face, still breathing heavily. 

“I don’t know what came over me! I only meant to ask a few questions to see what guys liked but then I just felt so horny talking to you…oh gods. I’m so embarrassed and now you must think I’m a terrible person because I like Fjord… and oh my gosh! You’ve seen me cum and now it will be so different between us…” Jester rambled in a mortified panic.

“Jester, Jester,” The Traveler said, stroking her arm. “You mustn’t worry about these things. How could I think any less of you? You are…spontaneous, instinctive…wildly passionate. This was merely an exercise in…anatomy, and you passed with flying colours. Why, I’d go so far as to say the lesson was a great success, highlighting skills I never knew you had. I only hope it was as enjoyable for you as it was for me.”

Sheepishly dropping her hands from her face and twirling circles with her finger on his shoulder,

“Oh, very much so, Traveler – the most fun I’ve had with my clothes on!” she chuckled and sighed all at once. “Sooo, you don’t mind that I uh, practiced on you?”

“Not in the slightest, Jester. I rather enjoyed myself.”

“I’m sorry about the wet patch on your trousers. I know I didn’t see it, but I can tell you have a really wonderful cock in there,” and she walked her fingers over his hip towards his lessening bulge. “It felt reeeally amazing.”

“Ah…thank you Jester,” he said with a hitch in his breath and chuckled at the enigmatic and unpredictable woman lying beside him. “Now, unless you have any more questions, I believe our time here is up for now and I ah, need to freshen up. Just, bear in mind though Jester, if you do choose to spend time with Fjord, or anyone else for that matter, remember, it’s not just about them. They would be lucky to have you.”

Jester grinned at The Traveler as he sat up, replacing his tunic and cloak.

“Thanks, Traveler. That really means a lot. And you never know, I might have questions again one day and need your help…unless you think you’d fall madly in love with me because, you know, I’m pretty great!” she beamed up at him, eyes narrowed and a wiggle of her eyebrows.

“You are indeed – always my favourite,” he said as he smiled, turned, and in the blink of an eye, was gone.

Jester lay there for a while, trying to fathom what had just happened, going over the noises The Traveler made, how his body responded to the different things she tried, how her body felt as she rubbed up against him. She wondered if Fjord would be the same and tried to imagine him undone lying beneath her. Only one way to find out…

**Author's Note:**

> First fanfic attempt so feel free to comment and leave your thoughts and/or feedback!
> 
> Don't forget to love each other! :D
> 
> Let chaos reign! :D


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